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It was shown that copolyimides based on adamantane-containing diamine and dianhydrides of 2,3,3′,4′-biphenyltetracarboxylic acid (a-BPDA) and 5,5′-(1,1,1,3,3,3-hexafluoropropane-2,2-diyl)bis(2-benzofuran-1,3-dione) (6FDA) are characterized by good thermal-oxidative properties (T5% = 465–485 °C) and a high optical transparency (T400 = 60–80%) in comparison with copolyimides based on the same dianhydrides and 2,2′-bis(trifluoromethyl)biphenyl-4,4′-diamine (TFBA), containing bulky trifluoromethyl fragments (T400 = 38–67%). [ABSTRACT FROM AUTHOR]

The Chan–Lam reaction conditions were optimized for the synthesis of N-aryl derivatives of adamantane-containing amines. A number of adamantane-containing amines and diamines with different steric hindrances at the primary amino groups were reacted with p-tolylboronic acid under the optimized conditions [0.1 M solution of amine in MeCN, p-tolylboronic acid (2 equiv), DBU (2 equiv), copper(II) acetate (20 mol %), 25°C, 24 h]. The reactivity of the amines was found to strongly depend on their structure, and the maximum yield of the target products reached 74% from the monoamines and 66% from the diamines. [ABSTRACT FROM AUTHOR]

N-(Het)arylation of adamantane-containing amines with halonaphthalenes and haloquinolines catalyzed by either CuI or copper nanoparticles with an average size of 25 nm in the presence of 2-isobutyrylcyclohexanone, rac-BINOL, and l-proline as a ligand and Cs2CO3 as a base in DMSO at 110 °C was studied. The reactions proceed smoothly with 2-iodonaphthalene and 6-iodoquinoline, the possibility of successful reactions with 6- and 3-bromoquinolines was also shown. In the case of 1-bromonaphthalene, 5- and 8-bromoquinolines, only Pd-catalyzed amination can provide the high yields of the products. An alternative possibility of C(sp2)—N bond formation was studied employing the Chan—Lam reaction with of 2-naphthaleneboronic acid and pinacolates of 6- and 3-quinolineboronic acids. [ABSTRACT FROM AUTHOR]

The N-heteroarylation of n-octylamine and adamantane-containing amines with 2-iodopyridine and 2-bromopyridine and its fluorinated derivatives under the catalysis of CuI and copper nanoparticles in DMSO in the presence of various ligands was studied. 2-Isobutyrylcyclohexanone was found to be the most efficient ligand in the reactions catalyzed by CuI. In the reactions catalyzed by copper nanoparticles, 2-isobutyrylcyclohexanone or l-proline turned to be most active. The yields of the reactions catalyzed by copper nanoparticles were better than or equal to those in the CuI-catalyzed processes. The possibility of nanocatalyst recycling was studied, and its reuse in 6 cycles without loss of activity was demonstrated. [ABSTRACT FROM AUTHOR]

Alkylation of N-aryl and N-arylalkyl acetamides with hydroxy adamantane derivatives in trifluoroacetic acid was studied. The differentiating effect of trifluoroacetic acid on the regio-selectivity of adamantylation of o-alkyl-substituted acetanilides was established, leading to energetically more stable products of para-substitution with respect to the alkyl group (the content of para-alkyl isomers is 93–94%). This enabled the synthesis of adamantylaminoarenes in 83–99% yields and with 95–99% purity. [ABSTRACT FROM AUTHOR]